| 01/20 | vs.  MAC Showcase@ Oak Park Ice Arena | Varsity B Hockey | 6:00 pm |
| 01/21 | vs. GS Race Day | Skiing | 4:00 pm |
| 01/22 | @ Spotlight Dual | Wrestling | 5:00 pm |
| 01/22 | vs. PHN@ Oak Park Ice Arena | Varsity Hockey | 6:00 pm |
| 01/23 | vs. Uof D/Ferndale | Swimming | 6:00 am |
| 01/23 | vs. Uof D/Ferndale | Swimming | 6:00 am |
| 01/23 | vs. Northville@ Oak Park Ice Arena | JV Hockey | 4:30 pm |
| 01/24 | vs. Royal Oak/Dexter/Fenton | Swimming | 6:00 am |
| 01/24 | vs. Orchard Lake St. Mary’s | Freshman Basketball | 4:00 pm |
| 01/24 | vs. Lake Forest Academy@ USA Arena | Varsity Hockey | 5:30 pm |
| 01/24 | vs. Orchard Lake St. Mary’s | JV Basketball | 5:30 pm |
| 01/24 | vs. Orchard Lake St. Mary’s | Varsity Basketball | 7:00 pm |
| 01/25 | @ Utica Invite (JV) | Wrestling | 9:00 am |
| 01/25 | @ Observerland Invite | Wrestling | 9:00 am |
| 01/25 | vs. Scrimmage Nubs Knob | Skiing | 10:00 am |
| 01/25 | vs. Scrimmage Nubs Knob | Skiing | 10:00 am |
| 01/25 | vs. St. Ignatius@ USA Arena | Varsity Hockey | 5:30 pm |
| 01/25 | vs. Turnpike League Playoff @ Taylor/Trenton | Varsity B Hockey | 6:00 pm |
| 01/27 | vs. CC VB@ Oak Park Ice Arena | Varsity B Hockey | 6:00 pm |
| 01/27 | vs. Salem@ Oak Park Ice Arena | Varsity Hockey | 6:00 pm |
| 01/28 | vs. SL Race Day | Skiing | 4:00 pm |
| 01/28 | vs. Toledo Central Catholic | Freshman Basketball | 4:00 pm |
| 01/28 | vs. Toledo Central Catholic | JV Basketball | 5:30 pm |
| 01/28 | vs. Toledo Central Catholic | Varsity Basketball | 7:00 pm |
| 01/29 | @ Walled Lake Northern | Wrestling | 5:00 pm |
| 01/30 | vs. Cranbrook | Swimming | 12:00 pm |
| 01/31 | vs. Don Thomas Cup @ Alpine | Skiing | 9:00 am |
| 01/31 | vs. Toledo St. John’s Jesuit | Freshman Basketball | 4:00 pm |
| 01/31 | @ Brighton | JV Hockey | 4:00 pm |
| 01/31 | vs. Houghton VB@ Oak Park Ice Arena | Varsity B Hockey | 5:00 pm |
| 01/31 | vs. Toledo St. John’s Jesuit | JV Basketball | 5:30 pm |
| 01/31 | vs. MIHL Showcase TBD @ Trenton | Varsity Hockey | 6:00 pm |
| 01/31 | vs. Toledo St. John’s Jesuit | Varsity Basketball | 7:00 pm |
| 02/01 | @ LW (VB) | Wrestling | 9:00 am |
| 02/01 | @ CHSL Championships | Wrestling | 9:00 am |
| 02/01 | vs. Turnpike League Playoff @ Trenton | Varsity B Hockey | 6:00 pm |
| 02/01 | vs. MIHL Showcase TBD @ Trenton | Varsity Hockey | 6:00 pm |
| 02/03 | vs. CHSL Championship @ Alpine Valley | Skiing | 2:00 pm |
| 02/04 | vs. Cranbrook@ Oak Park Ice Arena | JV Hockey | 4:00 pm |
| 02/04 | vs. L'anse Cruise North | Freshman Basketball | 4:00 pm |
| 02/04 | vs. L'anse Cruise North | JV Basketball | 5:30 pm |
| 02/04 | vs. Cranbrook@ Oak Park Ice Arena | Varsity Hockey | 6:00 pm |
| 02/04 | vs. L'anse Cruise North | Varsity Basketball | 7:00 pm |
| 02/05 | @ MHSAA Team District | Wrestling | 6:00 pm |
| 02/06 | vs. Alpine Valley Division Championships @ Alpine Valley | Skiing | 9:00 am |
| 02/07 | vs. U of D Jesuit@ Oak Park Ice Arena | JV Hockey | 4:30 pm |
| 02/07 | vs. U of D Jesuit@ Oak Park Ice Arena | Varsity Hockey | 6:30 pm |
| 02/08 | @ MHSAA Ind. District | Wrestling | 9:00 am |
| 02/08 | vs. Scrimmage Nubs Knob | Skiing | 10:00 am |
| 02/08 | vs. Oakland County | Swimming | 12:00 pm |
| 02/08 | @ Orchard Lake St. Mary’s | JV Hockey | 3:00 pm |
| 02/08 | vs. Orchard Lake St. Mary’s | Varsity B Hockey | 6:00 pm |
| 02/08 | vs. Orchard Lake St. Mary’s | Varsity Hockey | 7:30 pm |
| 02/10 | vs. MJVHL Playoffs@ Oak Park Ice Arena | JV Hockey | 6:00 pm |
| 02/11 | vs. MHSAA Regional 6 @ Alpine Valley | Skiing | 9:00 am |
| 02/12 | vs. MJVHL Playoffs@ Oak Park Ice Arena | JV Hockey | 6:00 pm |
| 02/12 | vs. Brighton@ Oak Park Ice Arena | Varsity Hockey | 6:00 pm |
| 02/12 | @ MHSAA Team Regional | Wrestling | 6:00 pm |
| 02/13 | vs. JV Open @ Alpine | Skiing | 12:00 pm |
| 02/15 | @ MHSAA Ind. Regional | Wrestling | 9:00 am |
| 02/15 | vs. MJVHL Playoffs | JV Hockey | 6:00 pm |
| 02/18 | vs. SEMSL Championship @ TBD | Skiing | 9:00 am |
| 02/18 | vs. DeLaSalle/Greenhills | Swimming | 6:00 pm |
| 02/21 | @ MHSAA Team State Finals | Wrestling | 9:00 am |
| 02/22 | @ MHSAA Team State Finals | Wrestling | 9:00 am |
| 02/24 | vs. MHSAA Div II State Championships @ Boyne Mt. | Skiing | 9:00 am |
| 02/27 | vs. CHSL Diving | Swimming | 12:00 pm |
| 02/28 | @ MHSAA Ind. State Finals | Wrestling | 9:00 am |
| 03/01 | @ MHSAA Ind. State Finals | Wrestling | 9:00 am |
| 03/01 | vs. MHSAA Quarterfinals @ TBD | Varsity Hockey | 6:00 pm |
| 03/06 | vs. MHSAA Semifinals@ USA Arena | Varsity Hockey | 6:00 pm |
| 03/07 | vs. CHSL Prelins | Swimming | 5:00 pm |
| 03/08 | vs. CHSL Finals | Swimming | 12:00 pm |
| 03/08 | vs. MHSAA Finals@ USA Arena | Varsity Hockey | 6:00 pm |
| 03/14 | vs. State Prelims | Swimming | 12:00 pm |
| 03/15 | vs. State Finals | Swimming | 12:00 pm |
MAC Showcase@ Oak Park Ice Arena
Orchard Lake St. Mary’s
Toledo Central Catholic
Toledo St. John’s Jesuit
U of D Jesuit@ Oak Park Ice Arena